(S)-tert-butyl 2,2-dimethyl-4-(((R,Z)-2,3,4,7-tetrahydrooxepin-3-yl)methyl)oxazolidine-3-carboxylate → (S)-tert-butyl 2,2-dimethyl-4-((R)-oxepan-3-ylmethyl)oxazolidine-3-carboxylate

HRID 451829Notes

Reaction equation

HRID 451829 reaction equation
[CH3:1][C:2]1([CH3:22])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([CH2:14][C@H:15]2[CH2:21][CH:20]=[CH:19][CH2:18][O:17][CH2:16]2)[CH2:4][O:3]1>CCO.[Ni]>[CH3:1][C:2]1([CH3:22])[N:6]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@@H:5]([CH2:14][C@H:15]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17][CH2:16]2)[CH2:4][O:3]1

Participants

4

Reactant 1

HCID 59201476(S)-tert-butyl 2,2-dimethyl-4-(((R,Z)-2,3,4,7-tetrahydrooxepin-3-yl)methyl)oxazolidine-3-carboxylate

Product 1

HCID 59201664(S)-tert-butyl 2,2-dimethyl-4-((R)-oxepan-3-ylmethyl)oxazolidine-3-carboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

The (S)-tert-butyl 2,2-dimethyl-4-(((R,Z)-2,3,4,7-tetrahydrooxepin-3-yl)methyl)oxazolidine-3-carboxylate was dissolved in EtOH, followed by the addition of Raney Ni. The mixture was hydrogenated at rt for 3 h. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to afford (S)-tert-butyl 2,2-dimethyl-4-((R)-oxepan-3-ylmethyl)oxazolidine-3-carboxylate (408 mg, 72%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3e6f842745a14de49e5395bed2d07cc1
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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